Set on five private acres in the heart of the Catskills, The Hilltop Hideaway is a grand countryside estate made for the big, once-in-a-while gatherings. Fourteen bedrooms, two full kitchens, and room after room to spread out give a large group everything it needs to come together and still find its own corners — the rare kind of place that works as well for a family reunion or milestone celebration as it does for a corporate retreat. The days here stretch out. Start with sunrise over the rolling hills, then fill the afternoon by the pool, in the hot tub, or trading rounds on the volleyball court and basketball hoop. As evening comes on, fire up the grill and settle in at the picnic tables for dinner under open sky, then drift to the outdoor fire and let the valley go quiet around you. Inside, warm wood finishes and rustic textures set a true lodge-style tone. The living areas are built to hold a crowd, with deep, comfortable seating, a grand stone fireplace anchoring the room, and multiple TVs ready for a movie night or a game day. Two full kitchens — stainless appliances, generous prep space, and dual dishwashers between them — take the strain out of cooking for a full house, whether that's one long shared dinner or a few smaller crews doing their own thing. The fun runs through every floor. A ping pong table waits outside for a casual match, while the main game room pulls everyone in with air hockey, foosball, card tables, and a full bar. Downstairs, the lower-level lounge opens a second bar alongside billiards and a Bluetooth sound system, and the attic keeps going with foosball, a poker table, and bubble hockey. A Sonos system runs through the main-floor living spaces, carrying the soundtrack from a slow morning right into the night. When it's time to turn in, fourteen well-appointed bedrooms across four floors give everyone room to breathe, sleeping up to 37 guests in all. Each one has its own character, from wood-paneled walls to quiet mountain outlooks. The setting brings it home. You're minutes from Hunter Mountain, its slopes practically part of the view — perfectly placed for skiing and tubing in winter, waterfall hikes and scenic drives come summer, and easygoing local dining all year, with Windham Mountain a short drive north. Spend the day chasing trails or do nothing more than take in the stillness of the hills; either way, The Hilltop Hideaway gives a big group all the space it needs to make the trip its own. AvantStay provides a personalized hospitality experience to elevate your stay. With our Concierge Service, guests have access to our tech-enabled services like fridge stocking, private chefs, massages, transportation, special occasion celebrations, baby gear rentals, ski gear, beach gear, and more. It's no wonder city dwellers flock to upstate New York's Catskill Mountains for a break from the daily grind. Its rural beauty and colorful foliage is a beautiful change of scenery. After all, it was here that inspired an entire artistic movement of Romantic painters to capture the area's rolling hills and pastoral setting. View the landscapes in person by hiking the Catskill Mountains, and then head to the farm to pick seasonal produce. Think apple picking in the fall and strawberries in the summer! Local Attractions: Windham Ski Mountain and Resort, Hunter Mountain Ski Resort, CD Lane Park, Windham Path, Windham High Peak, North Lake/South Lake hiking and kayaking area, Kaaterskill Falls, Hensonville’s farm-to-table market, Maplecrest trailheads, and the nearby towns of Tannersville, Catskill, and Hudson. Home Truths: Pool Heating — Please Read Before Booking The pool is heated with an electric heat pump, which works best in consistently warm weather. It runs 8–10 hours daily and heats the water gradually. During cooler periods (typically May–mid-June and after Labor Day in the Catskills), the pool may lose heat overnight faster than it can recover. As a result, it may not reach or maintain comfortable swimming temperatures. This is normal and not a malfunction. What to expect In early spring and late fall, the pool may be cooler than expected. Please plan accordingly. Pool season The pool typically opens in early May and needs about one week to be ready for swimming. It closes the weekend after Columbus Day. Guests booking near opening or closing dates should expect cooler conditions. - All bookings require a security deposit of $800 to be charged after booking. Event bookings and certain parties may require an additional security deposit. - This home allows up to 2 pets for a fee; undisclosed pets brought without AvantStay’s approval may result in a $500 fine per pet. - Pool heat is available at $150 per night. - The pool is open seasonally from Memorial Day through the weekend after Columbus Day. - Interested in hosting an event, prom, or undergraduate gathering? Reach out in advance to explore availability, options, and tailored pricing. - Guests must be 25 years or older to book this home. Parking Details: - Parking available for up to 15 cars. This is a smoke-free property. Violation of the no-smoking policy will result in forfeiture of the security deposit, a $300 smoking fee, and liability for any fire or property damage costs. As part of our commitment to being good neighbors, occupancy limits and quiet hours (9pm-8am) are strictly enforced. No speakers or sound systems will be provided for use in our properties. Violation of any noise ordinances will be subject to fines that can reach up to $10,000 per violation. Events or parties are not allowed without prior written approval and an additional fee. Any unauthorized parties or events will be shut down and a fine will be assessed. Please inquire for more information about our event policies and fees. There is nothing more important to us at AvantStay than the health, safety, and experience of our guests & staff. We've enhanced our cleaning and sanitation protocols and are taking extra care to disinfect all surfaces between reservations with hospital-grade disinfecting solutions. As a reminder, we do work with 3rd party vendors to maintain the property, and although we adhere to the strictest CDC guidelines and advise all contractors to wear PPE equipment, we can not always enforce. We strongly advise guests to please deny access if any vendors fail to meet and adhere to these standards. IDs will be requested for verification after booking. All bookings over 28 days require a security deposit. We report and prosecute all Credit Card Fraud.